lots of great input! thank you!
*IF* I went the 996 route, I'd probably wind up looking at someting arounda 2000 given my budget. I honestly think that from looking more closely at pricing of boxsters vs 911s - I'd be able to get a MUCH nicer boxster for the same money.
for example - for a 2000 model 911 I could easily spend $30k. For a boxster of the same year and mileage, I'd be closer to $20k for an S and even less for a base. For that same $30k, I'd be able to find a boxster far newer still under factory warranty.
I am looking for something fun. i'm not looking to drag race. I will probably take whatever I buy to a track on a RARE occasion. I can see myself doing a newbie track day event ONCE a year - something like that. I'd probably try to join the local porsche club and do some fun runs, or other driving events where you meet up, caravan around, drive some really cool roads, and eat lunch... i could take my 6 year old with me, drive the speed limit, but have a lot of fun on twisty roads, etc. the top down aspect of the boxster is a HUGE part of the appeal to me.
driving my dad's boxster - with the top down, on a sunny day, and listening to hte motor sing - with the wind blowing - was driving nirvana. i've never had more fun in a car than in his boxster - and his is just a 2.7. granted he has nice sticky 18" tires and M030 suspension..so it handles great...but it was just so much fun.
i think I'm going to focus on a boxster. the 996 would be "upscale/expensive" but I honestly don't know if it woul be more fun. I've driven my brother in law's 996 and i didn't like it as much as the boxster. his 996 is a 1998 or 1999 model...the interior is identical to my dad's boxster (my dad's 2000 has an upgrad 3 spoke steering wheel like the 911) - the 996 has more punch when I got on the gas...but the 996 did not feel as planted/glued down around turns. I felt like if I got on it too hard and too hot into turns that I was going to lose it. I also think his 996 had suspension that felt worn..the car pitched/dired under accel/braking whereas my dad's boxster is just planted hard no matter what. the 996 has less miles than the boxster too... maybe it was driven harder? dunno..
fun factor for twisty driving and top down fun _ i think a used boxster would give me way more bang for my buck than a used 996. and maybe cost me a LOT less to not only buy but maintain too.
pricewise - I am also probably going to have a hard time finding a clean nice 996 in my price range. i'd like to spend 25k or less. that would get me into a decent boxster. i'd LOVE tos pend about 20k and I know i can get a decent boxster - a 2000-2002 model in that range..maybe not an S..but a nice base for sure.
i'm going to do a bunch of research to see just how cheap I could find a nice S for. I'd be looking at 2000-2002 models. I *could* also look for 2003 base models, as they have a slight hp bump, would be a bit newer, and would somewhat in between a base and 00-02 S in terms of power.
thanks again guys!